Triphenylphosphine → tert-Butyl 5-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylate

HRID 1820245ノート

反応式

HRID 1820245 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:21])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[C:4]([CH2:22]O)[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:8]1([CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:12][CH2:13]1)[O:21][CH2:22]2

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 57889172tert-Butyl 4-(4-chloro-2-(hydroxymethyl)phenyl)-4-hydroxypiperidine-1-carboxylate

生成物 1

HCID 57889918tert-Butyl 5-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylate収率 97%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of tert-butyl 4-(4-chloro-2-(hydroxymethyl)phenyl)-4-hydroxypiperidine-1-carboxylate (1.3 g, 3.80 mmol) and triphenylphosphine (1.496 g, 5.70 mmol) in THF (20 mL) was treated with DEAD (0.903 mL, 5.70 mmol), and the mixture was stirred overnight at room temperature. The mixture was concentrated in-vacuo, and the residue was purified over silica gel, eluting with ethyl acetate/hexanes (5%-25% ethyl acetate), to yield the title compound (1.19 g, 3.67 mmol, 97% yield) as a colorless oil.

後処理

  1. concentrationThe mixture was concentrated in-vacuo
  2. customthe residue was purified over silica gel
  3. washeluting with ethyl acetate/hexanes (5%-25% ethyl acetate)

出典と根拠

ORDレコード
ord-d4bd90ccc25a4e43a4be793b1d2b00c5
出典データセット
uspto-grants-2009_10
特許番号
US07601844B2

反応ノート

読み込み中…