Methanol → HCID 15086785, compound

HRID 1710131Notes

Reaction equation

HRID 1710131 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[C:17](OC(=O)C)(=[O:19])[CH3:18].N1C=CC=CC=1.CO>CN(C)C1C=CN=CC=1.ClCCl>[C:17]([O:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1)(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 13438604Benzyl (3S)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 15086785HCID 15086785, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2.87 g of (S)-3-hydroxy-1-pyrrolidinecarboxylic acid, phenylmethyl ester, 2.0 ml of acetic anhydride, 2.0 ml of pyridine and 20 mg of 4-dimethylaminopyridine in 25 ml of dichloromethane was stirred for 72 hours. Methanol (2 ml) and dichloromethane (50 ml) were added. The dichloromethane solution was washed with 40 ml each of 1N hydrochloric acid and 5% sodium bicarbonate solution, dried, filtered and concentrated in vacuo. The residue was purified by chromatography (silica gel), giving 3.1 g of (S)-3-(acetyloxy)-1-pyrrolidinecarboxylic acid, phenylmethyl ester as a colorless oil, [α]D26 =+17° (dichloromethane).

Workup

  1. washThe dichloromethane solution was washed with 40 ml each of 1N hydrochloric acid and 5% sodium bicarbonate solution
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (silica gel)

Sources & evidence

ORD record
ord-c52bccb6d2824eb8ba00cddb187842f4
Source dataset
uspto-grants-1990_08
Patent number
US04952600

Reaction notes

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