Ethanol → HCID 66783309, compound

HRID 1096276Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:12][CH2:11][C:8]2([CH2:10][CH2:9]2)[C@H:7]([OH:13])[CH2:6]1.Br[CH2:15][CH:16]=[O:17].[C:18](=[O:21])([O-])[O-].[K+].[K+].[CH3:24]CO>>[CH3:18][O:21][CH:16]([O:17][CH3:24])[CH2:15][NH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:12][CH2:11][C:8]2([CH2:10][CH2:9]2)[C@H:7]([OH:13])[CH2:6]1

Participants

Reactant 4

HCID 702Ethanol

HCID 11430Potassium Carbonate

HCID 105131Acetaldehyde, bromo-

HCID 66783080HCID 66783080, compound

Product 1

HCID 66783309HCID 66783309, compound

Conditions

Temperature: 150 °C

Procedure

A mixture of (S)-6-(3-amino-propyl)-6-aza-spiro[2.5]octan-4-ol (200 mg, 1.09 mmol), bromoacetaldehyde (183 mg, 1.09 mmol), potassium carbonate (300 mg, 2.17 mmol), and EtOH (2.5 mL) was heated at 150° C. for 20 min under microwave irradiation, then insoluble material was removed by filtration and the filtrate evaporated to afford 224 mg of a 60:40 mixture of the title compound and the tertiary amine (S)-6-{3-[bis-(2,2-dimethoxy-ethyl)-amino]-propyl}-6-aza-spiro[2.5]octan-4-ol, which was directly used in the next step. Yellow gum, MS: 273.2 (M+H)+.

Workup

custominsoluble material was removed by filtration
customthe filtrate evaporated
customto afford

Sources & evidence

ORD record: ord-54295992e3464a97a0c00d6291fecb69
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138175B2

Reaction notes

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