2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → 6-Chloro-N-(cyclohexylmethyl)-2-[(3S)-3-[[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]amino]-1-piperidinyl]-5-quinolinecarboxamide

HRID 2217848Notes

Reaction equation

HRID 2217848 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:17]=[CH:16][C:15]3[C:14]([C:18]([NH:20][CH2:21][CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[O:19])=[C:13]([Cl:28])[CH:12]=[CH:11][C:10]=3[N:9]=2)[CH2:3]1.[Si:29]([O:36][CH2:37][CH:38]=O)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:28][C:13]1[CH:12]=[CH:11][C:10]2[N:9]=[C:8]([N:4]3[CH2:5][CH2:6][CH2:7][C@H:2]([NH:1][CH2:38][CH2:37][O:36][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH2:3]3)[CH:17]=[CH:16][C:15]=2[C:14]=1[C:18]([NH:20][CH2:21][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)=[O:19]

Participants

5

Reactant 3

HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59768630HCID 59768630, compound

Product 1

HCID 688096066-Chloro-N-(cyclohexylmethyl)-2-[(3S)-3-[[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]amino]-1-piperidinyl]-5-quinolinecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared according to the method of example 50(a) using 2-[(3S)-3-amino-1-piperidinyl]-6-chloro-N-(cyclohexylmethyl)-5-quinolinecarboxamide Example 51) (200 mg), activated 3 Å molecular sieves (0.20 g), (tert-butyldimethylsilyloxy)acetaldehyde (0.085 mL), dichloromethane (5.0 mL) and sodium triacetoxyborohydride (210 mg). Purification (SiO2, ethyl acetate:isohexane 1:1) gave the sub-titled compound (190 mg).

Workup

  1. customPrepared
  2. customPurification (SiO2, ethyl acetate:isohexane 1:1)

Sources & evidence

ORD record
ord-696ec5b01fa541c9be2a23f56865d369
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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