(+-)(2R,3S)-2-Methyl-2-nitro-1,3-butanediol → (+-)(2R,3S)-2-amino-2-methyl-1,3-butanediol acetate

Reaction equation

[C:1]([O:4][C@@H](C(N)(C)[C@H](O)C)C)(=[O:3])[CH3:2].[CH3:13][C@:14]([N+:20]([O-])=O)([C@@H:17]([OH:19])[CH3:18])[CH2:15][OH:16]>>[C:1]([OH:4])(=[O:3])[CH3:2].[NH2:20][C@@:14]([CH3:13])([C@@H:17]([OH:19])[CH3:18])[CH2:15][OH:16]

Participants

Reactant 2

HCID 13375424(+-)(2R*,3S*)-2-Methyl-2-nitro-1,3-butanediol

HCID 53919029(+-)(2R*,3RS,4R*)-3-Amino-3-methyl-2,4-pentanediol acetate

Product 1

HCID 86741966(+-)(2R*,3S*)-2-amino-2-methyl-1,3-butanediol acetateYield 93%

Procedure

Using the procedure described for 5D (+-)(2R*,3S*)-2-methyl-2-nitro-1,3-butanediol (6A) gave (+-)(2R*,3S*)-2-amino-2-methyl-1,3-butanediol acetate (93%) mp 163°-165° (C, H, N).

Sources & evidence

ORD record: ord-f25150674da54f408631b96d2ad3de75
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04810727

Reaction notes

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