Water → HCID 67793839, compound

HRID 1757283Notes

Reaction equation

HRID 1757283 reaction equation
[BH4-].[Li+].C([O:5][C:6]([C:8]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[N:33]=[N:34][N:35]([C:37]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[N:36]=3)=[CH:22][CH:21]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)=O)C.O>O1CCCC1>[OH:5][CH2:6][C:8]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[N:33]=[N:34][N:35]([C:37]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)[N:36]=3)=[CH:24][CH:25]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 19389895HCID 19389895, compound

Product 1

HCID 67793839HCID 67793839, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (11 mg) was added to a solution of 2-ethoxycarbonyl-4-([2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methoxy)quinoline (346 mg) in tetrahydrofuran (4 ml) and the mixture stirred for 18 hours. Water (20 ml) was added to the mixture and a white solid precipitated. The solid was collected by filtration, dissolved in ethyl acetate and the solution dried (MgSO4). The solvent was removed by evaporation and the residue crystallised from ethyl acetate/hexane to give 2-hydroxymethy-4-([2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methoxy)quinoline (213 mg), as a white crystalline solid, m.p. 183°-185° C. (dec.); NMR: 4.85(s,2H), 5.18(s,2H), 6.70(s,1H), 6.85-6.98(m,6H), 7.15-7.35(m,13H), 7.35-7.58(m,4H), 7.70(dt,1H), 7.95-8.08(m,2H), 8.15(d,1H); microanalysis, found: C,78.7; H,4.7; N,10.7%; C43H 33 N5O2 requires C,79.2; H,5.1; N,10.7%.

Workup

  1. customa white solid precipitated
  2. filtrationThe solid was collected by filtration
  3. dissolutiondissolved in ethyl acetate
  4. dry with materialthe solution dried (MgSO4)
  5. customThe solvent was removed by evaporation
  6. customthe residue crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e5a6e8f474174c3092cbef08ac3d3e52
Source dataset
uspto-grants-1995_08
Patent number
US05444071

Reaction notes

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