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

HRID 2209578Notes

Reaction equation

HRID 2209578 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3c250a460bb64abc867473110520abd7
Source dataset
uspto-grants-1995_10
Patent number
US05455246

Reaction notes

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