Hydrogen Bromide → HCID 73553822, compound

HRID 1733348Notes

Reaction equation

HRID 1733348 reaction equation
C([N:11]1[CH2:18][C:17]([F:20])([F:19])[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])(OCC1C=CC=CC=1)=O.[BrH:21].CCOCC>C(O)(=O)C>[BrH:21].[F:19][C:17]1([F:20])[CH2:18][NH:11][C@H:12]([C:13]([OH:15])=[O:14])[CH2:16]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 53909714(S)-1-((Benzyloxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid

Product 1

HCID 73553822HCID 73553822, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2.4 grams of N-carbobenzyloxy-4, 4-difluoro-L-proline and 12 ml. of hydrogen bromide in acetic acid (30-32%) is stirred for 30 minutes at room temperature and then 300 ml. of anhydrous ether is added. The mixture is cooled and the precipitated solid is filtered and dried under reduced pressure. The desired 4,4-difluoro-L-proline, hydrobromide melts at 163°-165° (s. 160°); [α]D26 -14° (c=1%; methanol).

Workup

  1. temperatureThe mixture is cooled
  2. filtrationthe precipitated solid is filtered
  3. customdried under reduced pressure
  4. customThe desired 4,4-difluoro-L-proline, hydrobromide melts at 163°-165° (s. 160°)

Sources & evidence

ORD record
ord-10bae7ba40fc41e8a8ddddb52859b125
Source dataset
uspto-grants-1980_12
Patent number
US04241076

Reaction notes

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