Formic Acid → HCID 67212121, compound

HRID 1401892Notes

Reaction equation

HRID 1401892 reaction equation
OC[C@@H]1CCC[NH2+]1.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:22][CH:21]=2)[C:16]([O-:18])=[O:17])=[CH:11][CH:10]=1.C(O)=O>C(OCC)(=O)C>[C:29]([O:28][C:26](=[O:27])[C:23]1[CH:24]=[CH:25][C:20]([CH2:19][C@H:15]([C:12]2[CH:13]=[CH:14][C:9]([Br:8])=[CH:10][CH:11]=2)[C:16]([OH:18])=[O:17])=[CH:21][CH:22]=1)([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 86676434HCID 86676434, compound

Product 1

HCID 67212121HCID 67212121, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirring slurry of 216.8 g of (R)-2-(4-Bromo-phenyl)-3-(4-tert-butoxycarbonyl-phenyl)-propionate (S)-2-hydroxymethyl pyrrolidinium in 2168 mL of ethyl acetate at 21° C. was treated 1084 mL of 10% aqueous formic acid. After 20 minutes, the separated organic phase was washed with water and dried over magnesium sulfate. The ethyl acetate solution was atmospherically displaced into heptanes to yield the product as a granular solid. 166.3 g (96% yield) of white solid, enantiomeric excess (“R” enantiomer) of 96.9% by chiral HPLC analysis as described above. HNMR: CDCl3, 1.50 (s, 9H), 2.96-3.00 (m, 1H), 3.32-3.37 (m, 1H), 3.73 (t, 1H), 7.03-7.08 (m, 4H), 7.35 (d, 2H), 7.76 (d, 2H)

Workup

  1. washthe separated organic phase was washed with water
  2. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-8b740187602240eab126d2de0e5363f0
Source dataset
uspto-grants-2014_12
Patent number
US08907103B2

Reaction notes

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