Pivalaldehyde → HCID 69465281, compound

HRID 2298560Notes

Reaction equation

HRID 2298560 reaction equation
[C:1]([N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]1=[O:14])(=[O:4])[CH2:2][CH3:3].[CH3:15][C:16]([CH3:20])([CH3:19])[CH:17]=[O:18]>>[OH:18][C@@H:17]([C:16]([CH3:20])([CH3:19])[CH3:15])[C@@H:2]([CH3:3])[C:1]([N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]1=[O:14])=[O:4]

Participants

3

Reactant 2

HCID 12417PivalaldehydeHCID 8437913-Propionyl-2-benzoxazolinone

Product 1

HCID 69465281HCID 69465281, compound

Procedure

Prepared according to the method of paragraph C by reaction of N-propionyl-2-benzoxazolone with trimethylacetaldehyde. Rapid addition of the aldehyde to the enolate solution at 0° C. gave a 1:1 ratio of the (2R*,3S*) and (2R*,3R*) isomers. The desired isomer was isolated by silica gel chromatography, then crystallized. 1H-NMR (CDCl3, 400 MHz) δ 8.05 (m, 1H), 7.20-7.27 (m, 4H), 4.24 (dq, J=7,4 Hz, 1H), 3.82 (br t, J=4 Hz, 1H), 2.33 (br d, J=4 Hz, 1H), 1.36(d, J=7 Hz, 3H), 0.99, (s, 9H). 13C-NMR (CDCl3, 100 MHz) δ 175.3, 150.8, 142.2, 127.9, 125.4, 124.9, 116.2, 109.9, 77.6, 40.3, 35.8, 29.7, 26.7, 12.7.

Workup

  1. customPrepared
  2. customgave a 1:1 ratio of the (2R*,3S*) and (2R*,3R*) isomers
  3. customThe desired isomer was isolated by silica gel chromatography
  4. customcrystallized

Sources & evidence

ORD record
ord-0790d1e168cb4b17a67ac6273b1c483d
Source dataset
uspto-grants-2002_12
Patent number
US06492562B1

Reaction notes

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