Sodium Hydroxide → HCID 42599377, compound

HRID 1958514Notes

Reaction equation

HRID 1958514 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:23](OC)=[O:24])=[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[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>[OH:24][CH2:23][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[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 68919114HCID 68919114, compound

Product 1

HCID 42599377HCID 42599377, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-phenyl-8H-3a-aza-cyclopenta[a]indene-1,2-dicarboxylic acid dimethyl ester (2.08 g, 6 mmol) in anhydrous dichloromethane (35 mL) was added dropwise to a stirred suspension of LiAlH4 (0.568 g, 15 mmol) in anhydrous ether (50 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 (2 mL), 15% NaOH aqueous solution (2 mL), and water (4 mL). The solid inorganic salt was filtered 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 yield (2-hydroxymethyl-3-phenyl-8H-3a-azacyclopenta[a]inden-1-yl)methanol (DA-1011), 1.24 g (71%): mp 169-171° C.; 1H NMR (DMSO-d6) δ3.93 (2H, s, CH2), 4.27 and 4.55 (each 2H, d, J=4.8 Hz, 2×CH2), 4.68 and 4.80 (each 1H, t, J=4.8 Hz, exchangeable, 2×OH), 6.73-6.74 (1H, m, ArH), 7.03-7.05 (1H, m, ArH), 7.09-7.12 (1H, m, ArH), 7.44-7.55 (6H, m, 6×ArH). Anal. Calcd. for C19H17NO2.0.3H2O: C, 76.90; H, 5.98; N, 4.72. Found: C, 76.89; H, 6.02; N, 4.56.

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

Sources & evidence

ORD record
ord-f77c14055b294eabbde787c9faf98983
Source dataset
uspto-grants-2013_04
Patent number
US08410130B2

Reaction notes

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