Ethyl formate → HCID 19771747, compound

HRID 1614591Notes

Reaction equation

HRID 1614591 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:28]=[N:29][N:30]([C:32]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[N:31]=3)=[CH:17][CH:16]=2)[C:10]2[CH2:9][NH:8][CH2:7][CH2:6][C:5]=2[N:4]=1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:57](OCC)=O.[OH-].[Na+]>O1CCCC1.O>[CH2:1]([C:3]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:28]=[N:29][N:30]([C:32]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[N:31]=3)=[CH:19][CH:20]=2)[C:10]2[CH2:9][N:8]([CH3:57])[CH2:7][CH2:6][C:5]=2[N:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8025Ethyl formateHCID 14798Sodium HydroxideHCID 19771694HCID 19771694, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19771747HCID 19771747, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-ethyl-5,6,7,8-tetrahydro-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,6-naphthyridine (500 mg) in dry tetrahydrofuran (THF) (2 ml) was added dropwise over a period of 20 minutes to a stirred suspension of lithium aluminium hydride (116 mg) in dry THF (2 ml) under an atmosphere of argon. The mixture was cooled to 0° C. and ethyl formate (173 mg) was added dropwise over a period of 10 minutes. The mixture was stirred for 1 hour and then water (0.12 ml), 4M sodium hydroxide solution (0.12 ml) and water (0.36 ml) were added successively. Stirring was continued for 10 minutes, and then insoluble material was removed by filtration and washed with ether (50 ml). The combined filtrate and washings were evaporated to dryness and the residue purified by flash chromatography, eluting with a mixture of methanol and dichloromethane (1:9 v/v). to give 2-ethyl-6-methyl-5,6,7,8-tetrahydro-4-[ (2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)-methoxy]-1,6-naphthyridine (240 mg), as a pale yellow solid, m.p. 143°-144° C.; NMR (d6 -DMSO, d4 -acetic acid): 1.2(t,3H), 2.65(q,2H), 2.95(s,4H), 3.65(s,2H), 5.15(s,2H), 6.8-6.9(m,7H), 7.1(d,2H), 7.3-7.7 (complex m,14H), 7.85(dd,1H).

Workup

  1. stirringStirring
  2. waitwas continued for 10 minutes
  3. custominsoluble material was removed by filtration
  4. washwashed with ether (50 ml)
  5. customThe combined filtrate and washings were evaporated to dryness
  6. customthe residue purified by flash chromatography
  7. washeluting with a mixture of methanol and dichloromethane (1:9 v/v)

Sources & evidence

ORD record
ord-e818fdde76cb4aeeb77314789009b72d
Source dataset
uspto-grants-1993_03
Patent number
US05198434

Reaction notes

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