Ethanolamine → 2-{[(4-Tert-butylphenyl)methyl]amino}ethan-1-ol

HRID 2244344Notes

Reaction equation

[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:13]([CH2:15][NH2:16])[OH:14].[BH4-].[Na+]>>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:16][CH2:15][CH2:13][OH:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 700Ethanolamine

HCID 703244-tert-Butylbenzaldehyde

HCID 4311764Sodium borohydride

Product 1

HCID 288330382-{[(4-Tert-butylphenyl)methyl]amino}ethan-1-olYield 93%

Procedure

The title compound was synthesized in analogy to example S3-C using 4-tert-butylbenzaldehyde (1000 mg, 6.17 mmol), ethanolamine (371 μl, 6.17 mmol) and sodium borohydride (350 mg, 9.25 mmol). The desired product (1190 mg, 93%) was isolated without further purification as a colourless oil. MS (ISP) 208.3 (M+H)+.

Sources & evidence

ORD record: ord-b567837ef5b7441eaae608acd6962b54
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678818B2

Reaction notes

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