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

HRID 2413586Notes

Reaction equation

HRID 2413586 reaction equation
[C:1](O[C@@H](C(N)(C)[C@H](O)C)C)(=[O:3])[CH3:2].[CH:13]([C:16]([N+:21]([O-])=O)([CH2:19][OH:20])[CH2:17][OH:18])([CH3:15])[CH3:14]>>[C:1]([O:18][CH2:17][C:16]([NH2:21])([CH:13]([CH3:15])[CH3:14])[CH2:19][OH:20])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 1438812-Nitro-2-isopropyl-1,3-propanediolHCID 53919029(+-)(2R*,3RS,4R*)-3-Amino-3-methyl-2,4-pentanediol acetate

Product 1

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

Procedure

Using the procedure in 5D, 2-isopropyl-2-nitro-1,3-propanediol (11A) gave 98% yield of 2-amino-2-isopropyl-1,3-propanediol acetate mp 155°-155.5°. 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-5cef9e61448e4c3e945ba32a0be39fa8
Source dataset
uspto-grants-1988_01
Patent number
US04719048

Reaction notes

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