Borane → 1-Cyclohexyl-4-(hydroxymethyl)pyrrolidin-2-one

HRID 2235179

Reaction equation

HRID 2235179 reaction equation
[CH:1]1([N:7]2[C:11](=[O:12])[CH2:10][CH:9]([C:13](O)=[O:14])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B.C1COCC1>C(Cl)Cl>[CH:1]1([N:7]2[CH2:8][CH:9]([CH2:13][OH:14])[CH2:10][C:11]2=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6331BoraneHCID 8028TetrahydrofuranHCID 2385461-Cyclohexyl-5-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 242755161-Cyclohexyl-4-(hydroxymethyl)pyrrolidin-2-oneYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Place 2-methylene-succinic acid (12.0 g, 92.2 mmol) and cyclohexylamine (9.15 g, 92.2 mmol) and heat to 160° C. for hours. Cool to give 18.8 g (96%) of 1-cyclohexyl-5-oxo-pyrrolidine-3-carboxylic acid. Charge a flask with 1-cyclohexyl-5-oxo-pyrrolidine-3-carboxylic acid (16.2 g, 76.7 mmol), add methylene chloride (20 mL) and cool to 0° C. Slowly add borane in THF (1M, 115.1 mL, 115.1 mmol) and stir for two hours at 0° C. Quench the reaction with ice and extract with methylene chloride. Dry over sodium sulfate, filter, and concentrate. Purify by silica gel (1-5% methanol in methylene chloride) to yield 9.9 g (65%) of the title compound: Mass spectrum (apci) m/z=198.1 (M+H).

Workup

  1. customQuench
  2. customthe reaction with ice
  3. extractionextract with methylene chloride
  4. dry with materialDry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by silica gel (1-5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-5319cd03529b4877a930954aa689ff61
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Linked notes

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