Methanol → (4S)-6-Azaspiro[2.5]octan-4-ol

HRID 559341Notes

Reaction equation

[C:1](OC(OC(OC(C)(C)C)=O)=O)([CH3:4])(C)[CH3:2].C([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])C.C[OH:24]>>[CH2:4]1[C:1]2([CH2:20][CH2:19][NH:18][CH2:21][C@H:22]2[OH:24])[CH2:2]1

Participants

Reactant 3

HCID 887Methanol

HCID 8471Triethylamine

HCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 44541813(4S)-6-Azaspiro[2.5]octan-4-ol

Procedure

The title compound was treated with di-tert-butyl-dicarbonate in methanol in the presence of triethylamine. The crude tert-butoxycarbonyl-protected amine product was analyzed by chiral GC (BGB-176; 30 m×0.25 mm; 80° C. to 210° C. in 43 min) and proved to be identical with intermediate 25b.

Sources & evidence

ORD record: ord-bf418f2836dd4c3f8687426e0d324a04
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063042B2

Reaction notes

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