Sodium Hydroxide → HCID 42599855, compound

HRID 1958518Notes

Reaction equation

HRID 1958518 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:27](OC)=[O:28])=[C:7]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:8]2[C:16]3[CH:15]=[CH:14][C:13]([O:17][CH3:18])=[CH:12][C:11]=3[CH2:10][C:9]=12)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[H-].[OH-].[Na+]>ClCCl.CCOCC.O>[OH:28][CH2:27][C:6]1[C:5]([CH2:3][OH:2])=[C:9]2[CH2:10][C:11]3[CH:12]=[C:13]([O:17][CH3:18])[CH:14]=[CH:15][C:16]=3[N:8]2[C:7]=1[C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 68914640HCID 68914640, compound

Product 1

HCID 42599855HCID 42599855, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 6-methoxy-3-(4-methoxyphenyl)-8H-3a-aza-cyclopenta[a]indene-1,2-dicarboxylic acid dimethyl ester (1.73 g, 3.56 mmol) in anhydrous dichloromethane (20 mL) was added dropwise to a stirred suspension of LiAlH4 (0.45 g, 11.85 mmol) in anhydrous ether (40 mL) at 0° C. The mixture was stirred for 15 min after the addition was completed. The excess hydride was carefully decomposed by the slow, sequential addition of water (1 mL), 15% NaOH aqueous solution (1 mL), and water (3 mL). The solid inorganic salt was removed by filtration and washed with dichloromethane. The combined filtrate and washings was concentrated in vacuo to dryness. The solid product was suspended in ether, collected by filtration, and dried to yield (2-hydroxymethyl-6-methoxy-3-(4-methoxyphenyl)-8H-3a-azacyclopenta[a]inden-1-yl)methanol (DA-1130), 1.35 g (91%): mp 186-187° C.; 1H NMR (DMSO-d6) δ 3.71 and 3.84 (each 3H, s, 2×OMe), 3.87 (2H, s, CH2), 4.24 and 4.53 (each 2H, d, J=4.4 Hz, 2×CH2O), 4.56 and 4.71 (each 1H, t, J=4.4 Hz, exchangeable, 2×OH), 6.64 (1H, d, J=8.7 Hz, ArH), 6.69 (1H, dd, J=2.5 Hz and J=8.7 Hz, ArH), 7.07 (2H, d, J=8.7 Hz, 2×ArH), 7.10 (1H, d, J=2.3 Hz, ArH), 7.40 (2H, d, J=8.7 Hz, 2×ArH). Anal. Calcd. for C21H21NO4.1.3H2O: C, 67.29; H, 6.29; N, 3.74. Found: C, 67.19; H, 5.90; N, 3.58.

Workup

  1. additionafter the addition
  2. customThe solid inorganic salt was removed by filtration
  3. washwashed with dichloromethane
  4. concentrationThe combined filtrate and washings was concentrated in vacuo to dryness
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-e7ca80a57e3046ddae28abdb9720e7de
Source dataset
uspto-grants-2013_04
Patent number
US08410130B2

Reaction notes

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