Hydrogen Bromide → HCID 69250178, compound

HRID 130619Notes

Reaction equation

HRID 130619 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.C(OC([N:22]1[CH2:26][CH2:25][C@H:24]([NH2:27])[C@@H:23]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=O)C1C=CC=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[BrH:48].C(Cl)[Cl:50]>C(O)(=O)C>[BrH:48].[BrH:48].[Cl:50][C:3]1[CH:2]=[C:1]([CH:6]=[CH:5][CH:4]=1)[CH2:11][NH:27][C@H:24]1[CH2:25][CH2:26][NH:22][C@H:23]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 86602376HCID 86602376, compound

Product 1

HCID 69250178HCID 69250178, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of cis-3-amino-2-phenyl-pyrrolidine-1-carboxylic acid benzyl ester p-toluenesulfonate (0.15 g, 0.32 mmol), obtained from preparatory example 6,3-chlorobenzaldehyde (0.34 mmol), and sodium triacetoxyborohydride (0.082 g, 0.38 mmol) was stirred in 3 mL of methylene chloride at rt for 16 h. The reaction was washed 1× with 1M NaOH, dried through cotton, and concentrated to give an oil. The oil was dissolved in acetic acid (1 mL) and a solution of 30% hydrogen bromide in acetic acid (0.302 g, 1.12 mmol) was added. The solution was stirred for 16 h and the resultant solids were collected, washed with ether, and concentrated under vacuum to give 0.114 g (79%) of the title compound. 1H NMR (2HBr, CD3OD) δ 7.72-7.68 (m, 2H), 7.64-7.57 (m, 3H), 7.45-7.31 (m, 4H), 5.31-5.29 (d, J=7.46 Hz, 1H), 4.45-4.41 (q, J=7.88 Hz, 1H), 4.31-4.28 (d, J=12.85 Hz, 1H), 4.04-4.01 (d, J=12.85 Hz, 1H), 3.97-3.91 (ddd, J=12.13, 9.33, 2.90 Hz, 1H), 3.62-3.54 (m, 1H), 2.89-2.81 (m, 1H), 2.66-2.56 (m, 1H). MS APCI: [M+H]+=287.2.

Workup

  1. washThe reaction was washed 1× with 1M NaOH
  2. customdried through cotton
  3. concentrationconcentrated
  4. customto give an oil
  5. customthe resultant solids were collected
  6. washwashed with ether
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5f94d3cb40764646ab4692bfb1ca8d13
Source dataset
uspto-grants-2008_06
Patent number
US07381741B2

Reaction notes

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