Tetrahydrofuran → HCID 178466616, compound

HRID 397172Notes

Reaction equation

HRID 397172 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C@@H:7]2[CH2:12][CH2:11][C@H:10]([N:13]3[CH2:17][CH2:16][CH2:15][C@H:14]3[CH2:18][NH2:19])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]=[C:32]=[O:33])(=O)C.C1C[O:37][CH2:36][CH2:35]1>>[C:36]([C:28]1[CH:27]=[C:26]([NH:31][C:32]([NH:19][CH2:18][C@@H:14]2[CH2:15][CH2:16][CH2:17][N:13]2[C@H:10]2[CH2:11][CH2:12][C@@H:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:21][CH:20]=3)[CH2:8][CH2:9]2)=[O:33])[CH:25]=[CH:30][CH:29]=1)(=[O:37])[CH3:35]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21916648HCID 21916648, compoundHCID 178511289HCID 178511289, compound

Product 1

HCID 178466616HCID 178466616, compound

Procedure

To a stirring solution of {(2S)-1-[cis-4-(4-fluorobenzyl)cyclohexyl]pyrrolidinyl}methanamine (58 mg, 2 mmol) in 2 ml of THF at 25° C. under N2 was added 3 acetylphenyl isocyanate (32 mg, 2 mmol Aldrich). Worked up after 4 hours by stripping off the THF then purifying over silica gel in 100% ethyl acetate followed by 4:1 chloroform/methanol. Obtained 11 mg of a white foam as product. MS (ESI) detects 452 (M+H).

Workup

  1. customthen purifying over silica gel in 100% ethyl acetate

Sources & evidence

ORD record
ord-534f23cf3ebf4514ad727869f1dc5855
Source dataset
uspto-grants-2003_08
Patent number
US06608227B1

Reaction notes

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