Hydrochloric Acid → HCID 54335685, compound

HRID 1700074Notes

Reaction equation

HRID 1700074 reaction equation
[O:1]=[C:2]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:3]([NH:5][CH3:6])=[O:4].Cl>CO.C(Cl)Cl>[OH:1][C@@H:2]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:3]([NH:5][CH3:6])=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 13355140HCID 13355140, compound

Product 1

HCID 54335685HCID 54335685, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The experiment was carried out in an analogous manner to Example 1. The asymmetric hydrogenation of 55.0 g (0.384 mol) of 2-keto-3,3,N-trimethyl-butyramide in 270 ml of methanol and 30 ml of methylene chloride in the presence of a catalyst prepared from 296 mg (0.384 mmol) of [Ru(OAc)2((S)-BIPHEMP)] and 31 ml of a 0.025 molar methanolic hydrochloric acid solution gave, after crystallization, 34.4 g (62%) of (S)-2-hydroxy-3,3,N-trimethyl-butyramide, m.p.=60-62° C., [α]=−59.9° (c=1, CHCl3), ee=99.2%.

Workup

  1. customgave
  2. customafter crystallization, 34.4 g (62%) of (S)-2-hydroxy-3,3,N-trimethyl-butyramide, m.p.=60-62° C., [α]=−59.9° (c=1, CHCl3), ee=99.2%

Sources & evidence

ORD record
ord-15a7b538dd284072a1e8b046786d3c00
Source dataset
uspto-grants-2002_02
Patent number
US06348612B1

Reaction notes

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