Benzoyl chloride → HCID 70024926, compound

HRID 1168590Notes

Reaction equation

HRID 1168590 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([Cl:22])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(OC)(C)(C)C>ClCCl>[ClH:22].[C:14]([O:13][C@H:10]1[CH2:11][CH2:12][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 15413tert-Butyl methyl etherHCID 2733875(S)-(-)-1-Benzyl-3-pyrrolidinol

Product 1

HCID 70024926HCID 70024926, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice cold, stirred solution of (S)-N-benzyl-3-pyrrolidinol (6.90 Kg, 38.9 mole) in dichloromethane (21 L), was slowly added a solution of benzoyl chloride (5.75 Kg, 40.8 mole) in dichloromethane (5 L). The reaction mixture was warmed to room temperature and stirred an additional two hours. Upon confirmation of reaction completion, methyl t-butyl ether (26 L) was added, and the resulting slurry was stirred for two hours at −10° C. The solids were isolated by filtration, washed with methyl t-butyl ether (14 L) and dried under vacuum at 40° C. to provide the title pyrrolidine (11.8 Kg, 96.6%) as a colorless crystalline material. mp 203-204° C.; 1H NMR (400 MHz, CDCl3) (major isomer) δ 8.14-7.90 (m, 2H), 7.70-7.39 (m, 8H), 5.59-5.58 (m, 1H), 4.30 (d, J=5.5 Hz, 2H), 4.14-4.08 (m, 1H), 3.80-3.76 (m, 1H), 3.24-3.17 (m, 2H), 2.66-2.61 (m, 1H), 2.37-2.32 (m, 1H); 13C NMR (100 MHz, CDCl3) δ 166.2, 165.6, 134.0, 133.7, 131.1, 130.9, 130.3, 130.2, 130.1, 130.0, 129.8, 129.6, 129.5, 129.4, 129.1, 129.0, 128.8, 128.6, 73.0, 71.9, 59.1, 58.5, 57.5, 57.2, 52.1, 52.0, 31.3, 30.6; MS [(m+1)/z] 282.2.

Workup

  1. additionwas added
  2. stirringthe resulting slurry was stirred for two hours at −10° C
  3. customThe solids were isolated by filtration
  4. washwashed with methyl t-butyl ether (14 L)
  5. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-80a1c2db73da4eecacd2cac56e56300d
Source dataset
uspto-grants-2003_09
Patent number
US06624313B2

Reaction notes

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