2-[3(S)-azido-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide → (3S,4aS,8aS)-2-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-tert-butyldecahydroisoquinoline-3-carboxamide

HRID 440116Notes

Reaction equation

HRID 440116 reaction equation
[N:1]([C@@H:4]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@H:5]([OH:24])[CH2:6][N:7]1[C@H:16]([C:17]([NH:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][C@H:14]2[C@H:9]([CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:8]1)=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][C@@H:4]([CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C@H:5]([OH:24])[CH2:6][N:7]1[C@H:16]([C:17]([NH:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH2:15][C@H:14]2[C@H:9]([CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:8]1

Participants

4

Reactant 1

HCID 100712032-[3(S)-azido-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide

Product 1

HCID 9865804(3S,4aS,8aS)-2-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-tert-butyldecahydroisoquinoline-3-carboxamideYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(A)(iii) A solution of 17 mg (0.04 mmol) of 2-[3(S)-azido-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide (prepared as described in Example 2 or Example 3) in 5 ml of ethanol was hydrogenated at about 3.4 atmospheres and at room temperature for 2 hours over 10 mg of 10% palladium-on-charcoal. The catalyst was filtered off and washed twice with ethanol. The combined filtrate and washings were evaporated to give 16 mg of 2-[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide; MS: m/e 402 [M+H]+.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed twice with ethanol
  3. customThe combined filtrate and washings were evaporated

Sources & evidence

ORD record
ord-e907ff84ff5740c9b6412bd65fbd96f4
Source dataset
uspto-grants-1996_05
Patent number
US05516913

Reaction notes

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