Acetic Acid → [3-Chloro-2-fluoro-5-(4-methoxy-piperidin-1-ylmethyl)-benzyl]-carbamic acid tert-butyl ester

HRID 1527496Notes

Reaction equation

HRID 1527496 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH:15]=O)[CH:12]=[C:11]([Cl:17])[C:10]=1[F:18])([CH3:4])([CH3:3])[CH3:2].CO[N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[C:28](O)(=[O:30])C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH2:15][N:22]2[CH2:23][CH2:24][CH:25]([O:30][CH3:28])[CH2:26][CH2:27]2)[CH:12]=[C:11]([Cl:17])[C:10]=1[F:18])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 198313851-MethoxypiperidineHCID 86673866HCID 86673866, compound

Product 1

HCID 68282992[3-Chloro-2-fluoro-5-(4-methoxy-piperidin-1-ylmethyl)-benzyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

was prepared according to Scheme C2 (step C) from (3-chloro-2-fluoro-5-formyl-benzyl)-carbamic acid tert-butyl ester (200 mg, 0.59 mmol), 1-methoxypiperidine (68 mg, 0.59 mmol), acetic acid (0.051 mL, 0.89 mmol) and sodium triacetoxyborohydride (313 mg, 1.5 mmol) in THF (8 mL). MS (LC-MS): 387.0 [M]+

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-c17b84e14ead4d1795312afaf1565982
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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