Sodium triacetoxyborohydride → HCID 178430549, compound

HRID 251114Notes

Reaction equation

HRID 251114 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][CH2:15][C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][N:17]=2)[CH2:10][CH2:9]1)(C)(C)C.[CH:25]([C:28]1[C:29]([CH:34]=O)=[N:30][CH:31]=[CH:32][CH:33]=1)([CH3:27])[CH3:26].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:22][C:21]1[C:16]([CH2:15][N:14]([CH2:34][C:29]2[C:28]([CH:25]([CH3:27])[CH3:26])=[CH:33][CH:32]=[CH:31][N:30]=2)[C@H:11]2[CH2:10][CH2:9][C@H:8]([NH2:7])[CH2:13][CH2:12]2)=[N:17][CH:18]=[C:19]([CH3:23])[CH:20]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 450836353-IsopropylpicolinaldehydeHCID 178430558HCID 178430558, compound

Product 1

HCID 178430549HCID 178430549, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of {trans-4-[(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-cyclohexyl}-carbamic acid tert-butyl ester and 3-isopropyl-pyridine-2-carbaldehyde in CH2Cl2 with NaBH(OAc)3 gave the desired amine as a white solid. Conversion to the HBr salt using General Procedure D gave COMPOUND 258 as an off-white solid. 1H NMR (D2O) δ 1.27 (d, 6H, J=7.0 Hz), 1.37-1.65 (m, 4H), 2.09-2.16 (m, 4H), 2.44 (s, 3H), 2.47 (s, 3H), 2.75 (t br, 1H, J=11.4 Hz), 3.16 (t br, 1H, J=11.4 Hz), 3.32 (h, 1H, J=7.0 Hz), 4.28 (s, 2H), 4.39 (s, 2H), 7.90 (dd, 1H, J=7.8, 5.1 Hz), 8.17 (s, 1H), 8.40 (s, 1H), 8.50 (d, 1H, J=7.8 Hz), 8.57 (d, 1H, J=5.1 Hz). 13C NMR (D2O) δ 17.22, 17.48, 22.15 (2), 25.97 (2), 28.28, 29.54 (2), 49.75, 50.31, 50.76, 60.49, 126.60, 137.17, 137.69, 138.19, 138.80, 144.83, 147.32, 148.03, 149.31, 150.12. ES-MS m/z 367 (M+H). Anal. Calcd. for C23H34N4.2.9HBr.1.7H2O: C, 43.72; H, 6.43; N, 8.87; Br, 36.68. Found: C, 43.94; H, 6.40; N, 8.48; Br, 36.43.

Sources & evidence

ORD record
ord-0fe5c897c704410d905f2d9dc1e8115a
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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