2-Nitro-2-isopropyl-1,3-propanediol → 2-Amino-2-isopropyl-1,3-propanediol acetate

Reaction equation

[C:1]([OH:4])(=[O:3])[CH3:2].N[C@@](C)([C@H](O)C)CO.[CH:13]([C:16]([N+:21]([O-])=O)([CH2:19]O)[CH2:17][OH:18])([CH3:15])[CH3:14]>>[C:1]([O:4][CH2:19][C:16]([NH2:21])([CH:13]([CH3:15])[CH3:14])[CH2:17][OH:18])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 1438812-Nitro-2-isopropyl-1,3-propanediol

HCID 86741969(+-)(2R*,3R*)-2-amino-2-methyl-1,3-butanediol acetate

Product 1

HCID 143912482-Amino-2-isopropyl-1,3-propanediol acetateYield 98%

Procedure

Using the procedure in 32E, 2-isopropyl-2-nitro-1,3-propanediol (63A) gave a 98% yield of 2-amino-2-isopropyl-1,3-propanediol acetate, mp 155°-155.5°, (C,H,N). H. S. Broadbent et al., J. Heterocyclic Chem. 13, 337 (1975) report the synthesis of this compound as the free base (mp 70°-72°).

Sources & evidence

ORD record: ord-90d84d8730184db996083c2f2aba76d1
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04910218

Reaction notes

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