3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (S)-(-)- → (R)-2-Amino-3-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}propan-1-ol

HRID 1401765Notes

Reaction equation

HRID 1401765 reaction equation
Br.[CH3:2][C:3]1([CH3:27])[CH2:12][CH2:11][C:10]([CH3:14])([CH3:13])[C:9]2[CH:8]=[C:7]([C:15]3[N:16]=[C:17]([N:20]4[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]4)[S:18][CH:19]=3)[CH:6]=[CH:5][C:4]1=2.C(OC([N:35]1[C@H:39]([CH:40]=O)[CH2:38][O:37]C1(C)C)=O)(C)(C)C.Cl.O1CCOCC1>>[NH2:35][C@H:39]([CH2:40][NH:26][CH:23]1[CH2:24][CH2:25][N:20]([C:17]2[S:18][CH:19]=[C:15]([C:7]3[CH:6]=[CH:5][C:4]4[C:3]([CH3:27])([CH3:2])[CH2:12][CH2:11][C:10]([CH3:13])([CH3:14])[C:9]=4[CH:8]=3)[N:16]=2)[CH2:21][CH2:22]1)[CH2:38][OH:37]

Participants

4

Reactant 3

HCID 1798243-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (S)-(-)-HCID 204431481,4-Dioxane hydrochlorideHCID 683809091-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamine hydrobromide

Product 1

HCID 53311112(R)-2-Amino-3-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}propan-1-ol

Procedure

The preparation is carried out starting from 1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamine hydrobromide and (S)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester. The protecting group is cleaved off by means of a 4N HCl/dioxane solution: The reaction mixture was stirred at room temperature for 2 h and evaporated to dryness. The product is converted into the hydrochloride by treatment with methanolic HCl.

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-fb9c3de5fd594843bf977bfca520ab88
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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