(3S,4aS,8aS)-N-(tert-Butyl)decahydroisoquinoline-3-carboxamide → (3S,4aS,8aS)-2-[(4S,5R)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl]-N-tert.-butyl-decahydro-isoquinoline-3-carboxamide

HRID 2209747Notes

Reaction equation

HRID 2209747 reaction equation
[CH2:1]([C@H:8]1[C@@H:12]([CH2:13]OS(C2C=CC(C)=CC=2)(=O)=O)[O:11][C:10](=[O:25])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([NH:30][C:31]([C@@H:33]1[CH2:42][C@H:41]2[C@H:36]([CH2:37][CH2:38][CH2:39][CH2:40]2)[CH2:35][NH:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>>[CH2:1]([C@H:8]1[C@@H:12]([CH2:13][N:34]2[C@H:33]([C:31]([NH:30][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:32])[CH2:42][C@H:41]3[C@H:36]([CH2:37][CH2:38][CH2:39][CH2:40]3)[CH2:35]2)[O:11][C:10](=[O:25])[NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 454736(3S,4aS,8aS)-N-(tert-Butyl)decahydroisoquinoline-3-carboxamideHCID 56996730p-toluenesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester

Product 1

HCID 11732686(3S,4aS,8aS)-2-[(4S,5R)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl]-N-tert.-butyl-decahydro-isoquinoline-3-carboxamideYield 63.4%

Procedure

Analogously to Example 1B), by reacting 7.2 g of p-toluenesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester (Example 11) with 4.8 g of N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide there are obtained 5.4 g (45%) of (3S,4aS,8aS)-2-[(4S,5R)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl]-N-tert.butyl-decahydro-isoquinoline-3-carboxamide p-tolylsuphonate, m.p. 202°-204° C.

Sources & evidence

ORD record
ord-8daab1c1ec8d4785ac407fde952b5f64
Source dataset
uspto-grants-1995_10
Patent number
US05455353

Reaction notes

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