Hydrochloric Acid → (4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride

HRID 559333Notes

Reaction equation

HRID 559333 reaction equation
C(OC([N:8]1[CH2:15][CH2:14][C:11]2([CH2:13][CH2:12]2)[C@H:10]([OH:16])[CH2:9]1)=O)(C)(C)C.[ClH:17].COC(C)(C)C>C(O)C>[ClH:17].[CH2:12]1[C:11]2([CH2:14][CH2:15][NH:8][CH2:9][C@H:10]2[OH:16])[CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15413tert-Butyl methyl etherHCID 66783172tert-Butyl (S)-4-hydroxy-6-azaspiro[2.5]octane-6-carboxylate

Product 1

HCID 44541812(4S)-6-Azaspiro[2.5]octan-4-ol hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (S)-4-hydroxy-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester (3.26 g, 14.3 mmol) in ethanol (10 ml) was treated at room temperature with hydrogen chloride solution (4 M in 1,4-dioxane, 30 ml), then after 1 h tert-butyl methyl ether (40 ml) was added. The suspension was stirred for 1 h, then the precipitate was collected by filtration to afford the title compound (2.11 g, 90%). White solid, MS: 128.1 (M+H)+.

Workup

  1. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-16cf333efc3743c0bd98b60a5016a15d
Source dataset
uspto-grants-2011_11
Patent number
US08063042B2

Reaction notes

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