HCID 21034112, compound → HCID 24904924, compound

HRID 1830727Notes

Reaction equation

HRID 1830727 reaction equation
C(OC([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:10]1)=O)(C)(C)C>C(O)=O>[NH2:8][C@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:10]1

Participants

3

Reactant 1

HCID 21034112HCID 21034112, compound

Product 1

HCID 24904924HCID 24904924, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of (3S)-3-(tert -butoxycarbonylamino)-1-(4-fluoro-benzyl)-pyrrolidine (400 mg, 1.36 mmol) was stirred in 15 mL of formic acid at room temperature. After 3 h, the clear colorless solution was concentrated to dryness and the residue was taken-up in 20 mL of EtOAc and washed with 10 mL of 5% NH40H, followed by 10 mL of brine. The solution was then dried over MgSO4, filtered and concentrated to give 240 mg (91%) of product, as a yellow oil. 1H-NMR (400 MHz, CDCl3) δ7.28 (m, 2H), 6.99 (m, 2H), 3.56 (d, J =6.2Hz, 2H), 3.47-3.53 (m, 1H), 2.67-2.71 (m, 2H), 2.42-2.48 (m, 1H), 2.28-2.31 (m, 1H), 2.21-2.28 (m, 1H), 1.59 (s, 2H, NH2), 1.43-1.52 (m, 1H).

Workup

  1. concentrationthe clear colorless solution was concentrated to dryness
  2. washwashed with 10 mL of 5% NH40H
  3. dry with materialThe solution was then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0bb44ce9ba69495596276ff7cc90ed96
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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