Benzyl Bromide → (3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]azetidin-2-one

HRID 247704ノート

反応式

HRID 247704 の反応式
[H-].[Na+].C([N:10]1[C@H:13](CCO)[C@@H:12]([C@H:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH3:18])[C:11]1=[O:27])C1C=CC=CC=1.C(Br)C1C=CC=CC=1>O.C1COCC1.CN(C)C=O>[Si:20]([O:19][C@@H:17]([C@@H:12]1[CH2:13][NH:10][C:11]1=[O:27])[CH3:18])([C:23]([CH3:26])([CH3:24])[CH3:25])([CH3:22])[CH3:21]

参加物

7

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 139595691-benzyl-3(S)-[1(R)-t-butyldimethylsilyloxyethyl]-4(R)-(2-hydroxyethyl)-2-azetidinone

生成物 1

HCID 10130795(3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]azetidin-2-one収率 58%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

There were added 1 ml of THF and 0.6 ml of dimethylformamide to 13 mg (0.26 mmol) of sodium hydride (oiliness: 50%), to which 2 ml of a THF solution of 64 mg (0.18 mmol) of 1-benzyl-3(S)-[1(R)-t-butyldimethylsilyloxyethyl]-4(R)-(2-hydroxyethyl)-2-azetidinone on the ice bath and the mixture was stirred for 10 minutes. Thereto 0.03 ml (0.25 mmol) of benzyl bromide was added and the mixture was stirred at room temperature for a night. The reaction mixture was added with water, extracted three times with diethyl ether, and the obtained extract was washed with a saturated aqueous solution of sodium chloride, dried with anhydrous magnesium sulfate and concentrated. The obtained residue was purified by 10 g of silica gel-column chromatography (eluent; hexane:diethyl ether=1:1) to give 46 mg of 1-benzyl-4(R)-2-benzyloxyethyl)-3(S)-[1(R)-t-butyldimethylsilyloxyethyl]-2-azetidinone (yield: 58%).

後処理

  1. extractionextracted three times with diethyl ether
  2. extractionthe obtained extract
  3. washwas washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified by 10 g of silica gel-column chromatography (eluent; hexane:diethyl ether=1:1)

出典と根拠

ORDレコード
ord-5529d26c64614193a5c8a7a4375d5f6c
出典データセット
uspto-grants-1987_11
特許番号
US04709064

反応ノート

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