Sodium Hydroxide → HCID 25256747, compound

HRID 1958511Notes

Reaction equation

HRID 1958511 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:19](OC)=[O:20])=[C:7]([CH2:17][CH3:18])[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].[H-].[OH-].[Na+]>ClCCl.CCOCC.O>[CH2:17]([C:7]1[N:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:10][C:9]2=[C:5]([CH2:3][OH:2])[C:6]=1[CH2:19][OH:20])[CH3:18]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 68914665HCID 68914665, compound

Product 1

HCID 25256747HCID 25256747, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-ethyl-8H-3a-aza-cyclopenta[a]indene-1,2-dicarboxylic acid dimethyl ester (2.5 g, 8.35 mmol) in anhydrous dichloromethane (30 mL) was added dropwise to a stirred suspension of LiAlH4 (0.793 g, 20.87 mmol) in anhydrous ether (30 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 (1.3 mL), 15% NaOH aqueous solution (1.3 mL), and water (3.6 mL). The solid inorganic salt was filtered and washed with dichloromethane. The combined filtrate and washings was concentrated in vacuo to dryness. The solid residue was triturated with ether, collected the solid product by filtration, and dried in vacuo to yield (3-ethyl-2-hydroxymethyl-8H-3a-azacyclopenta[a]inden-1-yl)-methanol (DA-1099), 1.31 g (64%): mp 131-133° C.; 1H NMR (DMSO-d6) δ 1.18 (3H, t, J=7.3 Hz, Me), 2.89 (2H, q, J=7.3 Hz, CH2), 3.81 (2H, s, CH2), 4.36 (2H, d, J=5.2, CH2O), 4.45 (2H, d, J=5.2 Hz, CH2O), 4.47 (1H, t, J=5.2 Hz, exchangeable, OH), 4.63 (1H, t, J=5.2 Hz, exchangeable, OH), 7.06-7.09 (1H, m, ArH), 7.30-7.34 (1H, m, ArH), 7.37-7.39 (1H, m, ArH), 7.45-7.46 (1H, m, ArH). Anal. Calcd for C15H17NO2: C, 74.05; H, 7.04; N, 5.76. Found: C, 73.22; H, 6.94; N, 5.71.

Workup

  1. additionafter the addition
  2. filtrationThe solid inorganic salt was filtered
  3. washwashed with dichloromethane
  4. concentrationThe combined filtrate and washings was concentrated in vacuo to dryness
  5. customThe solid residue was triturated with ether
  6. customcollected the solid product
  7. filtrationby filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-fcda781827aa4db5ac4df3e2bcec6339
Source dataset
uspto-grants-2013_04
Patent number
US08410130B2

Reaction notes

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