1,2-Dichloroethane → HCID 66970642, compound

HRID 1361518Notes

Reaction equation

HRID 1361518 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([C:8]2([O:14][CH3:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=1.[BH-](O[C:28]([CH3:30])=O)(OC(C)=O)OC(C)=O.[Na+].Cl[CH2:33][CH2:34]Cl>>[C@H:34]12[CH2:33][C@H:7]([CH:2]=[CH:3]1)[CH2:6][C@@H:28]2[CH2:30][N:11]1[CH2:10][CH2:9][C:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:16][CH3:17])([O:14][CH3:15])[CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 587722974-(5-Chloro-2-methoxyphenyl)-4-methoxypiperidine

Product 1

HCID 66970642HCID 66970642, compound

Procedure

4-(5-Chloro-2-methoxyphenyl)-4-methoxypiperidine 5d (51 mg, 0.2 mmol) was dissolved in 1,2-dichloroethane (1.5 mL) and treated with (S,S,S)-norbornene carboxaldehyde (24 mg, 0.2 mmol, 1.0 eq), followed by the addition of NaBH(OAc)3 (65 mg, 0.3 mmol, 1.5 eq). The reaction was allowed to stir at room temperature for 1 h, quenched with methanol (1 mL) and allowed to stir for another 30 min (until gas evolution stopped). The crude reaction mixture was purified by HPLC (10-99 CH3CN gradient, 0.05% TFA) to provide the desired product 1-(((1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl)methyl)-4-(5-chloro-2-methoxyphenyl)-4-methoxypiperidine (compound no. 140) as the TFA salt. LC/MS (RP-C18, 10-99% CH3CN/0.05% TFA gradient over 5 min) m/z 362.2 [M+H]+, retention time 2.53 min.

Workup

  1. customquenched with methanol (1 mL)
  2. stirringto stir for another 30 min (until gas evolution stopped)
  3. customThe crude reaction mixture
  4. customwas purified by HPLC (10-99 CH3CN gradient, 0.05% TFA)

Sources & evidence

ORD record
ord-1aa2781b4e1941ba860470fe5eea490a
Source dataset
uspto-grants-2011_02
Patent number
US07880007B2

Reaction notes

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