Triphenylphosphine → HCID 86610920, compound

HRID 2099374Notes

Reaction equation

CCOC(/N=N/C(OCC)=O)=O.[OH:13][C@@H:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1.[Cl:27][C:28]1[C:37]2[C:32](=[CH:33][C:34](O)=[C:35]([O:38][CH3:39])[CH:36]=2)[N:31]=[CH:30][N:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Cl:27][C:28]1[C:37]2[C:32](=[CH:33][C:34]([O:13][C@H:14]3[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]3)=[C:35]([O:38][CH3:39])[CH:36]=2)[N:31]=[CH:30][N:29]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Diethylazodicarboxylate (3.73 g) was added dropwise to a mixture of tert-butyl (3R)-3-hydroxypiperidine-1-carboxylate (4.29 g), 4-chloro-6-methoxyquinazolin-7-ol (3.00 g) and triphenylphosphine (5.61 g) in methylene chloride (75 ml). The solution was then heated to 0° C. and stirred for 3 hours. After cooling the mixture was filtered and then purified by flash column chromatography eluting with isohexane/acetone/triethylamine (80/20/1) to give tert-butyl (3S)-3-[(4-chloro-6-methoxyquinazolin-7-yl)oxy]piperidine-1-carboxylate as a colourless oil (3.29 g) which was used directly; Mass Spectrum: (M+H)+ 394.

Workup

temperatureAfter cooling the mixture
filtrationwas filtered
custompurified by flash column chromatography
washeluting with isohexane/acetone/triethylamine (80/20/1)

Sources & evidence

ORD record: ord-4ebe28be436a44bb8399c9b6ca20fe7b
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569577B2

Reaction notes

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