Pyridine → Tert-butyl 4-isocyanatobutanoate

HRID 1702802Notes

Reaction equation

C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[C:18]([O:22][C:23](=[O:30])[CH2:24][CH2:25][CH2:26]C(O)=O)([CH3:21])([CH3:20])[CH3:19].[N:31]1[CH:36]=CC=CC=1>>[C:18]([O:22][C:23]([CH2:24][CH2:25][CH2:26][N:31]=[C:36]=[O:8])=[O:30])([CH3:19])([CH3:20])[CH3:21]

Participants

Reactant 3

HCID 1049Pyridine

HCID 199401P,P-Diphenylphosphinic azide

HCID 114240215-(Tert-butoxy)-5-oxopentanoic acid

Product 1

HCID 20525055Tert-butyl 4-isocyanatobutanoate

Conditions

Temperature: 90 °C

Procedure

Diphenylphosphoryl azide (12.25 g.) was added dropwise to a solution of glutaric acid mono-tert-butyl ester (8.38 g.) in dry pyridine (37 ml.) and stirred at 90° C. for 40 minutes to give 3-tert-butoxycarbonylpropyl isocyanate (I.R.: 2270 cm-1).

Sources & evidence

ORD record: ord-10d23f7a3bde446d811e62e74643a032
Source dataset: uspto-grants-1982_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04349552

Reaction notes

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