Water → HCID 42599120, compound

HRID 1958508Notes

Reaction equation

HRID 1958508 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:18](OC)=[O:19])=[C:7]([CH3:17])[N:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:10][C:9]=12)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>ClCCl.CCOCC>[OH:19][CH2:18][C:6]1[C:5]([CH2:3][OH:2])=[C:9]2[CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[N:8]2[C:7]=1[CH3:17]

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 68919869HCID 68919869, compound

Product 1

HCID 42599120HCID 42599120, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methyl-8H-3a-azacyclopenta[a]indene-1,2-dicarboxylic acid dimethyl ester (3.14 g, 11 mmol) in anhydrous dichloromethane (30 mL) was added dropwise to a stirred suspension of LiAlH4 (1.04 g, 27.5 mmol) in anhydrous ether (45 mL) at 0° C. The mixture was stirred for 15 min after the addition was complete. The excess LiAlH4 was carefully decomposed by the slow, sequential addition of water (1.3 mL), 15% NaOH aqueous solution (1.3 mL), and water (3.6 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 residue was triturated with ether, the solid product was collected by filtration, and dried to give (2-hydroxymethyl-3-methyl-8H-3a-aza-cyclopenta-[a]inden-1-yl)methanol (DA-1090) 1.95 g (77%): mp 123-125° C.; 1H NMR (DMSO-d6) δ 2.53 (3H, s, Me), 3.80 (2H, s, CH2), 4.35 (2H, d, J=5.2 Hz, CH2O), 4.44 (2H, d, J=5.2 Hz, CH2O), 4.47 (1H, t, J=5.2 Hz, exchangeable, OH), 4.61 (1H, t, J=5.2 Hz, exchangeable, OH), 7.07-7.10 (1H, m, Hz, ArH), 7.29-7.33 (1H, m, ArH), 7.46-7.48 (2H, m, 2×ArH). Anal. Calcd. for C14H15NO2: C, 73.34; H, 6.59; N, 6.11. Found: C, 73.08; H, 6.59; N, 6.04.

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. customThe residue was triturated with ether
  6. filtrationthe solid product was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-8d10807a0d0d4f6a840f589bb748c52c
Source dataset
uspto-grants-2013_04
Patent number
US08410130B2

Reaction notes

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