Sodium Hydroxide → (3S,4aS,8aS)-2-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-tert-butyldecahydroisoquinoline-3-carboxamide

HRID 2292855Notes

Reaction equation

HRID 2292855 reaction equation
[CH2:1]([C@H:8]([NH:30]C(=O)OC)[C@H:9]([OH:29])[CH2:10][N:11]1[C@H:20]([C:21](=[O:28])[NH:22]OC(C)(C)C)[CH2:19][C@H:18]2[C@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[NH2:30][C@@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@H:9]([OH:29])[CH2:10][N:11]1[C@H:20]([C:21]([NH:22][C:2]([CH3:7])([CH3:3])[CH3:1])=[O:28])[CH2:19][C@H:18]2[C@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:12]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86750132methyl(1S,2R)-[1-benzyl-3-[(3S,4aS,8aS)-3-tert-butoxycarbamoyl-octahydro-isoquinolin-2-yl]-2-hydroxy-propyl]-carbamate

Product 1

HCID 9865804(3S,4aS,8aS)-2-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-tert-butyldecahydroisoquinoline-3-carboxamideYield 202.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A suspension of 41.37 g of methyl (1S,2R)-[1-benzyl-3-[(3 S,4aS,8aS)-3-tert-butoxycarbamoyl-octahydro-isoquinolin-2-yl]-2-hydroxy-propyl]-carbamate and 23.0 g of sodium hydroxide in 90 ml of ethanol and 90 ml of water was heated at reflux for 3.5 hours, diluted with 45 ml of water and cooled to 22% and the separated solid was filtered off, washed with a 1:4 mixture of ethanol/water and dried, there being obtained 35.35 g (98%) of pure 2-[3(S)-amino-2(R)-hydroxy-4-phenyl-butyl]-N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide, m.p. 173°-175° C. IR (KBr): 3435m, br. (NH, OH), 1665s (C=O), 1562m (amide II).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hours
  3. temperaturecooled to 22%
  4. filtrationthe separated solid was filtered off
  5. washwashed with a 1:4 mixture of ethanol/water
  6. customdried

Sources & evidence

ORD record
ord-41db402487db448e900e6b6e071bde25
Source dataset
uspto-grants-1997_11
Patent number
US05684176

Reaction notes

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