Hydrochloric Acid → Trans-benzyl (4-hydroxypyrrolidin-3-yl)carbamate hydrochloride

HRID 1666674Notes

Reaction equation

HRID 1666674 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@H:16]([OH:17])[CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:25]>C(Cl)(Cl)Cl.O1CCOCC1>[ClH:25].[OH:17][C@@H:16]1[CH2:15][NH:14][CH2:13][C@H:12]1[NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57970124trans-Tert-butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 86636483Trans-benzyl (4-hydroxypyrrolidin-3-yl)carbamate hydrochloride

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

t-Butyl (3R,4R)-3-benzyloxycarbonylamino-4-hydroxypyrrolidine-1-carboxylate (16 g) was dissolved in chloroform (143 mL), followed by addition of a solution (72 mL) of 4 M HCl in 1,4-dioxane, and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure to obtain benzyl ((3R,4R)-4-hydroxypyrrolidin-3-yl)carbamate mono hydrochloride. This compound was used in the subsequent step without purification.

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d7852294bded495e9a899ac71aebfd5c
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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