(4S)-2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde → (R)-3-{1-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}propane-1,2-diol

HRID 1401770Notes

Reaction equation

HRID 1401770 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.CC1(C)[O:33][C@H:32]([CH:34]=O)[CH2:31][O:30]1.Cl.CO>>[CH3:2][C:3]1([CH3:27])[CH2:12][CH2:11][C:10]([CH3:13])([CH3:14])[C:9]2[CH:8]=[C:7]([C:15]3[N:16]=[C:17]([N:20]4[CH2:25][CH2:24][CH:23]([NH:26][CH2:34][C@@H:32]([OH:33])[CH2:31][OH:30])[CH2:22][CH2:21]4)[S:18][CH:19]=3)[CH:6]=[CH:5][C:4]1=2

Participants

4

Reactant 3

HCID 11105390(4S)-2,2-Dimethyl-1,3-dioxolane-4-carboxaldehydeHCID 21893726Hydrochloride methanolHCID 683809091-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamine hydrobromide

Product 1

HCID 53311189(R)-3-{1-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}propane-1,2-diol

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)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde. The protecting group is cleaved off by means of a 1.25 N HCl/methanol solution: The reaction mixture was stirred at room temperature for 5 h, evaporated to dryness and dried under a high vacuum. The product was converted into the hydrochloride by treatment with methanolic HCl.

Workup

  1. customevaporated to dryness
  2. customdried under a high vacuum

Sources & evidence

ORD record
ord-bc356112555e465d870e490c91847d65
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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