Aluminium lithium hydride → (S)-benzyl 5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-ylcarbamate

HRID 473104노트

반응식

HRID 473104 반응식
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:21](OC)=[O:22])[CH:18]=2)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:22][CH2:21][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[CH2:13][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:20]2

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 67025433(S)-methyl 2-(benzyloxycarbonylamino)-2,3-dihydro-1H-indene-5-carboxylate

생성물 1

HCID 70224068(S)-benzyl 5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-ylcarbamate수율 82%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To (S)-methyl 2-(benzyloxycarbonylamino)-2,3-dihydro-1H-indene-5-carboxylate (7.38 mmol, 2.4 g) at 0° C. in THF (36.9 mL) under an argon atmosphere was added Lithium aluminium hydride in THF (7.38 mmol, 7.38 mL) dropwise. The reaction was left to stir for 1.5 hrs at 0 degrees. The reaction was quenched with water before the addition of 5N HCl (aq) to adjust the pH to 3. DCM was added before separating the aqueous and washing once with water and once with brine. The DCM layer was dried over MgSO4 before removing the solvent in vacuo. The crude product was purified by silica chromatography (2:1 Heptane/EtOAc to 2:1 EtOAc/Heptane, 100 g silica cartridge) to give the product as a white solid (1.8 g, 82%). 1H NMR (400 MHz, CDCl3) δ 1.60 (t, 1H), 2.81 (m, 2H), 3.27 (m, 2H), 4.53 (d, 1H), 4.66 (d, 2H), 4.95 (brs, 1H), 5.12 (s, 2H), 7.17 (d, 2H), 7.23 (m, 1H), 7.33 (m, 5H).

후처리

  1. waitThe reaction was left
  2. customThe reaction was quenched with water before the addition of 5N HCl (aq)
  3. additionDCM was added
  4. custombefore separating the aqueous and
  5. washwashing once with water and once with brine
  6. dry with materialThe DCM layer was dried over MgSO4
  7. custombefore removing the solvent in vacuo
  8. customThe crude product was purified by silica chromatography (2:1 Heptane/EtOAc to 2:1 EtOAc/Heptane, 100 g silica cartridge)

출처 및 근거

ORD 기록
ord-3aad87eb262c450f9240905618a42c4a
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633237B2

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