Lithium naphthalenide → (1R,2R,5R*)-8-Benzyl-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol

HRID 2088097

反応式

[C-]1C2C(=CC=CC=2)C=CC=1.[Li+].[CH2:12]([N:19]1[C@@H:24]2[C@H:25](S(C3C=CC=CC=3)(=O)=O)[CH2:26][C@@:20]1([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C@H:21]([OH:36])[CH2:22][CH2:23]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[CH2:12]([N:19]1[C@@H:24]2[CH2:25][CH2:26][C@@:20]1([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C@H:21]([OH:36])[CH2:22][CH2:23]2)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

実験手順

Lithium naphthalenide (200 ml, 0.6M in teterahydrofuran) was added dropwise into a −78° C. solution of (1R*,2R*,5S*,6R*)-8-benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol (Description 4; 25 g, 57.7 mmol) in THF (350 ml). The mixture was quenched by addition of saturated ammonium chloride and warmed to room temperature The reaction mixture was partitioned between ethyl acetate and saturated ammonium chloride. The organic layer was washed (×2) with water then dried (MgSO4), filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 5, 15 and 40% ethyl acetate/iso-hexanes to yield the title compound (14.3 g, 84.6%).

後処理

customThe mixture was quenched by addition of saturated ammonium chloride
customwas partitioned between ethyl acetate and saturated ammonium chloride
washThe organic layer was washed (×2) with water
dry with materialthen dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel eluting with 5, 15 and 40% ethyl acetate/iso-hexanes

出典と根拠

ORDレコード: ord-161e92622f60454e9cc151d3e58bf2c2
出典データセット: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US06727249B2

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 1

実験手順

後処理

出典と根拠

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