HCID 57303202, compound → HCID 57087530, compound

HRID 2396153Notes

Reaction equation

HRID 2396153 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C@@H:17]([OH:32])[CH2:18][CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)(=O)C.[Pt]=O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C@@H:17]([OH:32])[CH2:18][CH:19]([CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1)[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1)[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 57303202HCID 57303202, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57087530HCID 57087530, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of (2S,3S)-2-t-butoxycarbonylamino-1-cyclohexyl-5,5-diphenyl-3-hydroxypentane (0.74 g) in acetic acid (50 ml) was hydrogenated over platinum oxide (0.2 g) at 3 atmospheric pressure of hydrogen gas for 2 hours at 37° C. The solution was filtered and concentrated in vacuo to give (2S,3S)-2-t-butoxycarbonylamino-3-hydroxy-1,5,5-tricyclohexylpentane (753 mg) as an oil. Rf: 0.72 (n-hexane:ethyl acetate, 2:1, V/V)

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce3bdb85960a4679acf0d9bd54efad25
Source dataset
uspto-grants-1996_02
Patent number
US05491132

Reaction notes

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