tert-butyl {(3R)-1-[4-hydroxy-4-(2-isopropyl-1,3-thiazol-5-yl)cyclohexyl]pyrrolidin-3-yl}carbamate → 4-[(3R)-3-Aminopyrrolidin-1-yl]-1-(2-isopropyl-1,3-thiazol-5-yl)cyclohexanol

HRID 1025759Notes

Reaction equation

HRID 1025759 reaction equation
[OH:1][C:2]1([C:21]2[S:25][C:24]([CH:26]([CH3:28])[CH3:27])=[N:23][CH:22]=2)[CH2:7][CH2:6][CH:5]([N:8]2[CH2:12][CH2:11][C@@H:10]([NH:13]C(=O)OC(C)(C)C)[CH2:9]2)[CH2:4][CH2:3]1>Cl.O1CCOCC1>[NH2:13][C@@H:10]1[CH2:11][CH2:12][N:8]([CH:5]2[CH2:4][CH2:3][C:2]([C:21]3[S:25][C:24]([CH:26]([CH3:28])[CH3:27])=[N:23][CH:22]=3)([OH:1])[CH2:7][CH2:6]2)[CH2:9]1

Participants

3

Reactant 1

HCID 59556180tert-butyl {(3R)-1-[4-hydroxy-4-(2-isopropyl-1,3-thiazol-5-yl)cyclohexyl]pyrrolidin-3-yl}carbamate

Product 1

HCID 595561434-[(3R)-3-Aminopyrrolidin-1-yl]-1-(2-isopropyl-1,3-thiazol-5-yl)cyclohexanolYield 105.2%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

The mixture of tert-butyl {(3R)-1-[4-hydroxy-4-(2-isopropyl-1,3-thiazol-5-yl)cyclohexyl]pyrrolidin-3-yl}carbamate (0.50 g, 1.22 mmol) in 4 N HCl/dioxane (10 mL) was stirred at room temperature for 1 hour. The solution was concentrated to give 0.397 g of the title compound as 2 HCl salt. MS (EI) calcd: (M+1)+=309.2; found: 310.2.

Workup

  1. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-2732bb32ed97409da2bd890e8d657fb4
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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