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

HRID 1627562노트

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HRID 1627562 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-95f7646c3828436ca9bec9e8800a72bb
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785632B2

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