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Trifluoroacetic acid → 4-Amino-1-[(9S,10S)-2-chloro-9,10-dihydro-9,10-methanoanthracen-9-yl-carbonyl]piperidine

HRID 2209578
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HRID 2209578 반응식
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C@:15]23[CH2:30][C@H:22]([C:23]4[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][C:28]=42)[C:21]2[C:16]3=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=[O:35].[OH-].[Na+]>C(Cl)Cl>[NH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([C@:15]23[CH2:30][C@H:22]([C:23]4[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][C:28]=42)[C:21]2[C:16]3=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:35])[CH2:10][CH2:9]1
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참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 57094261HCID 57094261, 화합물

생성물 1

HCID 572905474-Amino-1-[(9S,10S)-2-chloro-9,10-dihydro-9,10-methanoanthracen-9-yl-carbonyl]piperidine수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of t-butyl-N-(1-[(9S,10S)-2-chloro-9,10-dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)carbamate produced in Example 1b (1.24 g, 2.74 mmol) in methylene chloride (15 mL) was added trifluoroacetic acid (2.11 mL, 27.37 mmol). After stirring the resulting mixture for 18 h, the reaction was concentrated to give a pale pink syrup. The syrup was dissolved in methylene chloride (100 mL), cooled to 0 C. (ice bath) and treated with 3N sodium hydroxide and extracted with methylene chloride (3×50 mL). The combined extracts was washed with 3N sodium hydroxide (2×75 mL) and brine (75 mL), dried (sodium sulfate), filtered, and concentrated to give the title compound as a white foamy glass (967 mg, 100%); mp 93°-5° C.; MS(CI); 353 (M+H); NMR (300 MHz,DMSO-d6): 1.23(br m, 2H), 1.67-1.85(br m, 2H), 2.71-3.02(br m, 5H), 3.27-3.39(br m, part. submerged, 2H), 3.66(br s, 1H), 4.42(s, 1H), 4.47(s, 1H), 7.00(m, 3H), 7.30-7.66(br m, 4H).

후처리

  1. concentrationthe reaction was concentrated
  2. customto give a pale pink syrup
  3. temperaturecooled to 0 C
  4. extractionextracted with methylene chloride (3×50 mL)
  5. washThe combined extracts was washed with 3N sodium hydroxide (2×75 mL) and brine (75 mL)
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3c250a460bb64abc867473110520abd7
출처 데이터셋
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05455246

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