Methanol → 2-(Hydroxymethyl)adamantane-2-carbonitrile

HRID 1849770노트

반응식

HRID 1849770 반응식
[C:1]([C:3]1([C:13](OC)=[O:14])[CH:10]2[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2)#[N:2].CO.[BH4-].[Li+]>O1CCCC1>[OH:14][CH2:13][C:3]1([C:1]#[N:2])[CH:4]2[CH2:12][CH:8]3[CH2:7][CH:6]([CH2:11][CH:10]1[CH2:9]3)[CH2:5]2

참가 물질

5

반응물 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 21609112Methyl 2-cyanoadamantane-2-carboxylate

생성물 1

HCID 867036522-(Hydroxymethyl)adamantane-2-carbonitrile수율 91.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 2-cyanoadamantane-2-carboxylate (1.33 g, 6.07 mmol) in anhydrous tetrahydrofuran (50 mL) was added anhydrous methanol (0.49 mL, 12 mmol) and lithium borohydride (4.0 M solution in tetrahydrofuran, 3.0 mL, 12 mmol). The mixture was heated to reflux under a nitrogen atmosphere for 7 hours, cooled to ambient temperature and quenched with careful addition of saturated aqueous ammonium chloride (10 mL). The mixture was diluted with ethyl acetate (200 mL), washed with a 3:1 mixture of saturated aqueous ammonium chloride and water (2×200 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the title compound (1.06 g, 91%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 3.92 (s, 2H), 2.24-2.20 (m, 2H), 2.10-1.97 (m, 4H), 1.86-1.84 (m, 5H), 1.73-1.64 (m, 4H); MS (ES−) m/z 192.2 (M+1).

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux under a nitrogen atmosphere for 7 hours
  3. customquenched with careful addition of saturated aqueous ammonium chloride (10 mL)
  4. additionThe mixture was diluted with ethyl acetate (200 mL)
  5. washwashed with a 3:1 mixture of saturated aqueous ammonium chloride and water (2×200 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e2fdfe6780e349958453dbe534189468
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952169B2

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