Methanol → tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

HRID 1627562ノート

反応式

HRID 1627562 の反応式
[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][CH:3]([C:5](OC)=[O:6])[CH2:2]1.CO.[Li+].[BH4-].O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1.CCOC(C)=O>[OH:6][CH2:5][CH:3]1[CH2:4][N:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2]1

参加物

7

反応物 4

HCID 887MethanolHCID 2724148Sodium potassium tartrate tetrahydrateHCID 4148881Lithium borohydrideHCID 446076271-tert-Butyl 3-methyl azetidine-1,3-dicarboxylate

生成物 1

HCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate収率 73.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

1-tert-butyl 3-methyl azetidine-1,3-dicarboxylate (1055 mg, 4.90 mmol) was dissolved in THF (17 mL) and then cooled to 0° C. MeOH (0.397 mL, 9.80 mmol) and LiBH4 (14.7 mmol) were added sequentially. The reaction was warmed to room temperature over 3 h. Then 10% aqueous potassium sodium tartrate tetrahydrate (Rochelle's Salt) (30 mL) and EtOAc (30 mL) were added and the solution stirred at room temperature over 30 minutes. The organic layer was separated and then dried (Na2SO4) and concentrated to afford 674 mg of t-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (1-3) as a crude product (clear oil). The product was used directly in the next step without purification.

後処理

  1. temperatureThe reaction was warmed to room temperature over 3 h
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-95f7646c3828436ca9bec9e8800a72bb
出典データセット
uspto-grants-2014_07
特許番号
US08785632B2

反応ノート

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