(3aS,4R,7aR)-2,2-dimethylhexahydro-1,3-benzodioxol-4-amine → ((3aS,4R,7aR)-2,2-dimethylhexahydrobenzo-1,3-dioxol-4-yl)-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]-piperidin-4-yl}amine

HRID 1401861Notes

Reaction equation

HRID 1401861 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]2[CH2:7][CH2:8][CH2:9][C@@H:10]([NH2:11])[C@@H:4]2[O:3]1.[CH3:13][C:14]1([CH3:38])[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[C:20]2[CH:19]=[C:18]([C:26]3[N:27]=[C:28]([N:31]4[CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]4)[S:29][CH:30]=3)[CH:17]=[CH:16][C:15]1=2>C1COCC1>[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]2[CH2:7][CH2:8][CH2:9][C@@H:10]([NH:11][CH:34]3[CH2:35][CH2:36][N:31]([C:28]4[S:29][CH:30]=[C:26]([C:18]5[CH:17]=[CH:16][C:15]6[C:14]([CH3:38])([CH3:13])[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[C:20]=6[CH:19]=5)[N:27]=4)[CH2:32][CH2:33]3)[C@@H:4]2[O:3]1

Participants

4

Reactant 2

HCID 58369647(3aS,4R,7aR)-2,2-dimethylhexahydro-1,3-benzodioxol-4-amineHCID 673225751-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-one

Product 1

HCID 67323175((3aS,4R,7aR)-2,2-dimethylhexahydrobenzo-1,3-dioxol-4-yl)-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]-piperidin-4-yl}amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The preparation is carried out analogously in THF starting from 27 mg (0.16 mmol) of (3aS,4R,7aR)-2,2-dimethylhexahydrobenzo-1,3-dioxol-4-ylamine and 60 mg (0.16 mmol) of 1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-one. The purification is carried out by means of flash chromatography on silica gel.

Workup

  1. customThe purification

Sources & evidence

ORD record
ord-ad8674b999f24b9db3b136dc718b9884
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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