Hydrogen Bromide → HCID 69249317, compound

HRID 130620Notes

Reaction equation

HRID 130620 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]=[C:30]([Cl:34])[CH:29]=1)=O)C1C=CC=CC=1.[C:35](O[BH-](OC(=O)C)OC(=O)C)(=[O:37])C.[Na+].[BrH:49]>C(Cl)Cl.C(O)(=O)C>[BrH:49].[BrH:49].[Cl:34][C:30]1[CH:29]=[C:28]([C@H:23]2[C@@H:24]([NH:27][CH2:11][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=3[O:37][CH3:35])[CH2:25][CH2:26][NH:22]2)[CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 5049666Sodium triacetoxyborohydrideHCID 86602377HCID 86602377, compound

Product 1

HCID 69249317HCID 69249317, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of cis-3-amino-2-(3-chloro-phenyl)-pyrrolidine-1-carboxylic acid benzyl ester p-toluenesulfonate (0.32 mmol), obtained from preparatory example 7,2-methoxy-benzaldehyde (0.034 g, 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. Trituration with hot isopropanol provided 0.082 g (50%) of title compound. 1H NMR (2HBr, CD3OD) δ 7.72 (s, 1H), 7.63-7.59 (m, 3H), 7.44-7.40 (t, J=7.89 Hz, 1H), 7.31-7.29 (d, J=7.48 Hz, 1H), 7.04-7.02 (d, J=8.31 Hz, 1H), 6.99-6.96 (t, J=7.48 Hz, 1H), 5.25-5.23 (d, J=7.47 Hz, 1H), 4.39-4.33 (q, J=7.47 Hz, 1H), 4.26-4.23 (d, J=12.86 Hz, 1H), 4.13-4.10 (d, J=12.86 Hz, 1H), 3.93-3.87 (ddd, J=12.0, 9.55, 3.74 Hz, 1H), 3.81 (s, 3H), 3.59-3.51 (m, 1H), 2.81-2.74 (m,1H), 2.66-2.58 (m, 1H). MS APCI: [M+H]+=317.3

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-950639fa6c2f48e2a989d77d5657ca73
Source dataset
uspto-grants-2008_06
Patent number
US07381741B2

Reaction notes

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