Trityl chloride → (2R,4R)-4-Hydroxy-1-trityl-pyrrolidine-2-carboxylic acid methyl ester

HRID 2217456ノート

反応式

HRID 2217456 の反応式
C[O:2][CH:3]1[CH2:7][N:6](C(O)=O)[CH:5]([C:11]([OH:13])=[O:12])[CH2:4]1.[CH2:14](N(CC)CC)C.[C:21]1([C:27](Cl)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)(Cl)Cl>[CH3:14][O:13][C:11]([C@H:5]1[CH2:4][C@@H:3]([OH:2])[CH2:7][N:6]1[C:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:12]

参加物

5

反応物 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 221815244-Methoxy-pyrrolidine-1,2-dicarboxylic acid

生成物 1

HCID 68685802(2R,4R)-4-Hydroxy-1-trityl-pyrrolidine-2-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

Into a solution of 1 (10 g, 55 mmol) in anhydrous CHCl3 (100mL) was added triethylamine (19 mL, 138 mmol) and triphenylmethyl chloride (14.5 g, 52 mmol). The mixture was stirred at RT for 3d before concentrating and redissolving in EtOAc. The solution was washed sequentially with 10% aq. citric acid, water, and brine before drying over MgSO4 and concentrating under reduced pressure to reveal 2 (20 g, 100%) as a yellow solid.

後処理

  1. concentrationbefore concentrating
  2. dissolutionredissolving in EtOAc
  3. washThe solution was washed sequentially with 10% aq. citric acid, water, and brine
  4. dry with materialbefore drying over MgSO4
  5. concentrationconcentrating under reduced pressure

出典と根拠

ORDレコード
ord-8698f54160d54676bcc2df18a0340936
出典データセット
uspto-grants-2008_08
特許番号
US07407972B2

反応ノート

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