Hydrochloric Acid → 4-Cyclohexyl-l-proline

HRID 1732120Notes

Reaction equation

HRID 1732120 reaction equation
C(OC([N:11]1[CH2:15][C@H:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:13][C@H:12]1[CH2:22][OH:23])=O)C1C=CC=CC=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:25].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.Cl>CN(C)C=O>[CH:16]1([CH:14]2[CH2:15][NH:11][C@H:12]([C:22]([OH:23])=[O:25])[CH2:13]2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724130Cornforth reagentHCID 13648262(2S-trans)-1-[(Benzyloxy)carbonyl]-4-cyclohexyl-2-pyrrolidinemethanol

Product 1

HCID 186648034-Cyclohexyl-l-proline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S-trans)-1-[(benzyloxy)-carbonyl]-4-cyclohexyl-2-pyrrolidinemethanol (0.65 g) in dimethylformamide (10 ml) was added pyridinium dichromate (2.1 g). The mixture was stirred at room temperature for 16 hours and poured onto crushed ice and hydrochloric acid (25 ml). Extraction with ethyl acetate followed by solvent evaporation yielded 0.4 g of (trans)-1-[benzyloxy)carbonyl]-4-cyclohexyl-L-proline as a thick oil. The compound can be deprotected using catalytic hydrogenation as described in Method V.

Workup

  1. additionpoured
  2. extractionExtraction with ethyl acetate
  3. customfollowed by solvent evaporation

Sources & evidence

ORD record
ord-a0793f0a994847b792f8353a874b7733
Source dataset
uspto-grants-1986_11
Patent number
US04625038

Reaction notes

Loading…