Sodium Hydroxide → 1-(Phenylmethyl) (2S,4R)-4-fluoro-1,2-pyrrolidinedicarboxylate

HRID 1733351Notes

Reaction equation

HRID 1733351 reaction equation
[C:1]([N:11]1[CH2:19][C@H:18]([F:20])[CH2:17][C@H:12]1[C:13]([O:15]C)=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[OH-].[Na+]>CO>[C:1]([N:11]1[CH2:19][C@H:18]([F:20])[CH2:17][C@H:12]1[C:13]([OH:15])=[O:14])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 140362011-Benzyl 2-methyl (2S,4R)-4-fluoropyrrolidine-1,2-dicarboxylate

Product 1

HCID 537322451-(Phenylmethyl) (2S,4R)-4-fluoro-1,2-pyrrolidinedicarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the procedure of Example 19(d), the methyl ester product from part (d) is saponified with 11.5 ml. of 2 N sodium hydroxide in 50 ml. methanol to give 5.3 g. of the desired product as a pale yellow viscous oil. This material is converted to the cyclohexylamine salt by treatment with 2 g. of cyclohexylamine in 25 ml. of ethanol. 4.7 g. of cyclohexylamine salt are obtained; m.p. 188°-191° (s. 183°); [α]D25 -42° (c=1%, methanol). Crystallization from 55 ml. of isopropanol gives 3.7 g. of colorless cyclohexylamine salt; m.p. 194°-196° (s. 187°); [α]D25 -44° (c=1%, methanol).

Sources & evidence

ORD record
ord-217031021ad244a3bed2c4f3d02c419f
Source dataset
uspto-grants-1980_12
Patent number
US04241076

Reaction notes

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